Fuel oil compositions containing an n-alkyl aminopropionitrile salt of an alkyl phosphoric acid ester



United States Patent FUEL OIL COMPOSITIONS CONTAINING AN N- ALKYL AMINOPROPIONITRILE SALT OF AN ALKYL PHOSPHORIC ACID ESTER Arthur Cizek, Bellaire, Tex., assignor to Armour and Company, Chicago, 11]., a corporation of Delaware No Drawing. Filed Aug. 22, 1962, Ser. No. 218,545

6 Claims. (Cl. 44--72) This invention relates to fuel oil compositions, and more particularly to a composition for inhibiting corrosion in refinery-type fuel oils, including diesel oils, jet fuels, turbine oils, etc.

Hydrocarbon fuel oils, such as those used in diesel and combustion engines, turbines, and in various storage and tank systems, present corrosion problems and have other shortcomings due to chemical deterioration. This is particularly true of fuel oils which contain a substantial quantity of cracked components. I have discovered that by incorporating in the fuel oil an N-alkyl aminopropionitrile salt of monoand/or di-alkyl acid phosphoric acid ester into the fuel oil system to be protected, there is effective inhibition of such corrosion and chemical deterioration.

A primary object, therefore, of the invention is to provide a fuel oil composition effective for inhibition of such corrosion, degradation or deterioration. A further object is to provide as corrosion inhibitors in refinery-type oils, N-alkyl aminopropionitrile salts of alkyl phosphoric acid esters. A further object is to provide an improved fuel oil composition which is protective of an oil system employing the fuels. Other specific objects and advantages will appear as the specification proceeds.

In one embodiment of my invention, I incorporate a minor proportion of an oil-soluble non-emulsifying N- alkyl aminopropionitrile salt of a monoor di-alkyl acid phosphoric acid ester into the oil system to be protected. I prefer to employ from about ppm. to 60 ppm. of the salt. Best results have been obtained when the salt constitutes about 40 parts to a million parts of the fuel oil. Compounds effective for the purposes of my invention have the following structure:

where R is an aliphatic hydrocarbon chain having from 8 to 18 carbon atoms, where R" is an aliphatic hydrocarbon chain having from 4 to 12 carbon atoms, and where R is selected from the group consisting of hydrogen and an aliphatic hydrocarbon chain having from 4 to 12 carbon atoms.

Examples of radicals coming within the definition of R include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl,

and mixtures of hydrocarbon radicals as derived from tallow, soybean oil, coconut oil, and other animal and vegetable oils.

The hydrocarbon distillate fuel oils in which the active chemical ingredients of this invention are incorporated may be treated or untreated cracked fuel oils or mixtures of cracked fuels with straight run fuel oils, straight run fuel oils, said fuel oils having components normally distilling from about 300 F. to about 700 F. Such hydrocarbon distillates include diesel fuel oils, jet fuel oils, turbine oils, cracked gas oils, burner oils, kerosene, and mixtures of such cracked fuels with the corresponding or like straight run hydrocarbon fractions.

Specific example illustrative of embodiments of the invention may be set out as follows:

EXAMPLES Dynamic tests which represent a modification of the steam turbine oil test were carried on with respect to a number of additives to fuel oil, the conditions, procedures, etc. being as follows.

(1) Test conditions:

Hydrocarbon medium, isooctane Corrodant, synthetic sea water Room temperature, 72-80 F. for 20 hrs.

(2) Apparatus: As shown in ASTM Manual for Method D-665 using SAE 1020 steel.

(3) Polishing of specimen rods: As indicated in Method (4) Procedure: 300 ml. of isooctane were added to each beaker and also the desired amount of additive. In this case, 30 and p.p.m. of chemical were used. The stirrer and clean-ed specimen rod were inserted at this time. The control (just isooctane) and the treated products were then stirred continuously for 30 minutes to insure wetting the rod. At this point in the test, 30 m1. of synthetic sea water were added. The controls and treated products were then stirred continuously for 20 hours. At the end of 20 hours, the test was stopped and the steel specimen rods removed. The rods were then inspected for corrosion and rate by Humble Oil Co. designation.

Humble Oil Co. rating designation The conditions and results are set out in the following table:

DYNAMIC CORROSION TEST IN ISOOCTANE The designation "Armeen TD in the above examples indicates distilled tallow amine.

While in the foregoing specification I have set out specific compositions and ingredients in considerable detail for the purpose of illustrating embodiments of the invention, it will be understood that such detail or details may be varied widely by those skilled in the art without departing from the spirit of my invention.

I claim:

1. An improved fuel oil composition, comprising fuel oil and an oil soluble non-emulsifying N-alkyl aminopropionitrile salt of an alkyl phosphoric acid ester in the proportion of about 560 parts of said salt to one million parts of fuel oil.

2. An improved fuel oil composition, comprising fuel oil and a substance selected from the group consisting of an oil soluble non-emulsifying N-alkyl aminopropionitrile salt of a monoand di-alkyl acid phosphoric acid ester in the proportion of 5-60 parts of said salt to one million parts of fuel oil.

3. An improved fuel oil composition, comprising fuel oil and an N-alkyl aminopropionitrile salt of an alkyl phosphoric acid ester having the following structure:

Where R is an aliphatic hydrocarbon chain having from 8 to 18 carbon atoms, Where R is an aliphatic hydrocarbon chain having from 4 to 12 carbon atoms, and where 4- R is selected from the group consisting of hydrogen and an aliphatic hydrocarbon chain having from 4 to 12 carbon atoms, the proportion of said salt being 5-60 parts per million parts of fuel oil.

4. The composition of claim 3 in which the proportion of the salt is about parts of the salt per million parts of fuel oil.

5. An improved fuel oil composition, comprising fuel oil and oil-soluble non-emulsifying N-alkyl aminopropionitrile salt of mono-alkyl acid phosphoric acid ester in the proportion of about 5-60 parts of said salt to one million parts of fuel oil.

6. An improved fuel oil composition, comprising fuel oil and oil-soluble non-emulsifying N-alkyl aminopropionitrile salt of di-alkyl acid phosphoric acid ester in the the proportion of about 5-60 parts of said salt to one million parts of fuel oil.

References Cited by the Examiner UNITED STATES PATENTS 1/54 Bishop 252389 8/58 Chenicels 44--74 DANIEL E. WYMAN, Primary Examiner. 

1. AN IMPROVED FUEL OIL COMPOSITION, COMPRISING FUEL OIL AND AN OIL SOLUBLE NON-EMULSIFYING N-ALKYL AMINOPROPIONITRILE SALT OF AN ALKYL PHOSPHORIC ACID ESTER IN THE PROPORTION OF ABOUT 5-60 PARTS OF SAID SALT TO ONE MILLION PARTS OF FUEL OIL. 